Nucleophilic, radical, and electrophilic (phenylsulfonyl)difluoromethylations

Hu, Jinbo

doi:10.1016/j.jfluchem.2009.05.016

Cited by 137 publications

(25 citation statements)

References 46 publications

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“…The SCF 2 H-containingm olecules have also been shown to be uniquelye ffective in bioactive compounds. [29] To our delight, CF 2 HSOCl was successfully synthesized by using CF 2 HSO 2 Na (see the Experimental Section for details). Next, we soughtt oe xtend the reaction scope for difluoromethylthiolation (Table10).…”

Section: Resultsmentioning

confidence: 99%

Trifluoromethanesulfinyl Chloride for Electrophilic Trifluoromethythiolation and Bifunctional Chlorotrifluoromethythiolation

Jiang

Yan

Wang

et al. 2018

Chemistry A European J

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Trifluoromethanesulfinyl chloride (CF3SOCl) has been introduced as a new reagent for C−H trifluoromethylthiolation of indoles, thiophenes, and ketones under catalyst‐free conditions and in the absence of reductant. The disproportionation of CF3SOCl to CF3SO2Cl and CF3SCl provides two pathways for the trifluoromethylthiolation. Direct trifluoromethylthiolation with CF3SCl or trifluoromethylsulfoxidation with CF3SOCl is followed by reduction with CF3SOCl. This reagent can be used to functionalize benzothiophenes, benzofurans, and indenes under the promotion of Ag2CO3. It can also be used for trifluoromethylthiolation of thiols and benzeneselenols, and 1,2‐bifunctional chlorotrifluoromethylthiolation of indoles, styrenes, and alkyenes. The method can also be extended for difluorometylthiolation reactions using CF2HSOCl.

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Section: Resultsmentioning

confidence: 99%

Trifluoromethanesulfinyl Chloride for Electrophilic Trifluoromethythiolation and Bifunctional Chlorotrifluoromethythiolation

Jiang

Yan

Wang

et al. 2018

Chemistry A European J

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“…When highlighting the excellent stereoselectivity of the addition reaction between compound 1 and different sugar lactones, the preference for beta ‐configuration could be attributed to the sterically demanding difluoromethyl group. (2) Reduction of difluoromethyl‐2‐pyridyl or ‐phenyl sulfone to the –CF 2 H structure is generally performed with amalgam or samarium reagents 9a. From the synthetic viewpoint, our one‐pot reduction with a Grignard reagent is less known, highly practical, and very efficient for the syntheses of 1‐deoxy‐1‐difluorinated 2‐ketose analogues.…”

Section: Resultsmentioning

confidence: 99%

Highly Stereoselective Nucleophilic Addition of Difluoromethyl‐2‐pyridyl Sulfone to Sugar Lactones and Efficient Synthesis of Fluorinated 2‐Ketoses

Liu¹,

Yin²,

Yin³

et al. 2014

Eur J Org Chem

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Nucleophilic addition of difluoromethyl‐2‐pyridyl sulfone to sugar lactones proceeded with good yield and excellent stereoselectivity. The hitherto unknown direct addition intermediates are stable and capable of useful conversions: Formal elimination of the anomeric hydroxy and sulfonyl groups yielded a 1‐deoxy‐1‐difluoromethylene mannopyranose derivative. Directly from sugar lactones, by nucleophilic addition and subsequent one‐pot reduction with allylmagnesium chloride, unprecedented fluorinated 2‐ketose analogues were prepared efficiently.

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“…Therefore, much effort has been made to develop novel and efficient methods to introduce the difluoromethyl group into molecules [7,8]. The ethyl difluoroacetoacetate is a commercially available difluorinated building block, which can undergo several reactions to form difluoromethyl-containing compounds [8][9][10]. However, little is known about the reactivity, properties and products of this useful difluoro-containing building block when it is used as a component in the multicomponent reactions which is a powerful tool for the construction of diverse and complex molecules.…”

Section: Introductionmentioning

confidence: 99%

An efficient three-component domino synthesis of difluoromethyl-containing 1,4-dihydropyridines under solvent and catalyst free conditions

Cao

et al. 2010

Sci. China Chem.

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The difluoromethyl-containing Hantzsch 1,4-dihydropyridines were synthesized in good yields by a one-pot cyclocondensation of ethyl difluoroacetoacetate (EDFAA), a variety of aromatic aldehydes and ammonium acetate under solvent and catalyst free conditions. The comparison of reaction conditions and products was made among the different 1,3-carbonyl substrates (ethyl acetoacetate, ethyl difluoroacetoacetate and ethyl trifluoroacetoacetate) for the Hantzsch reaction. three-component, difluoromethyl, 1,4-dihydropyridines, ethyl difluoroacetoacetate

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Nucleophilic, radical, and electrophilic (phenylsulfonyl)difluoromethylations

Cited by 137 publications

References 46 publications

Trifluoromethanesulfinyl Chloride for Electrophilic Trifluoromethythiolation and Bifunctional Chlorotrifluoromethythiolation

Trifluoromethanesulfinyl Chloride for Electrophilic Trifluoromethythiolation and Bifunctional Chlorotrifluoromethythiolation

Highly Stereoselective Nucleophilic Addition of Difluoromethyl‐2‐pyridyl Sulfone to Sugar Lactones and Efficient Synthesis of Fluorinated 2‐Ketoses

An efficient three-component domino synthesis of difluoromethyl-containing 1,4-dihydropyridines under solvent and catalyst free conditions

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